Q – I just started managing a new team and one of my staff members is close friends with my boss. I keep noticing them having personal powwows and secret strategy sessions without me. And there have been a couple times where I’m pretty sure he was actively undermining me. I’m feeling very frustrated and pretty powerless in this situation. What are your tips for managing an insubordinate staff member?

A – Yikes. I’m not going to sugar coat this for you, managing the type of insubordination you’re describing is tricky – not impossible – but certainly a challenge. I’ve had the misfortune of having to work through a couple of these situations in my career and I’m painfully aware of just how exasperating it can be. To get through it with your career intact you have to strike an extremely delicate balance. You need to be strong without being defensive. You need to be aware without becoming paranoid. It’s the kind of career obstacle that will test even the most seasoned manager.

In my experience, the best first step to managing the situation is to understand what brand of insubordination you’re dealing with. Here are a few of the common scenarios you should be on the lookout for. Each one demands a carefully thought out strategy to overcome.

The CEO’s brother in-law just got moved onto your team. And he’s incompetent. How the heck are you supposed to hold him accountable without getting into hot water?

You just took over a new team and your boss’s best friend from college is on it. How do you get her to respect you and follow direction?

You’ve got an overly ambitious staff member with a habit for going straight to your manager with ideas and suggestions. How much is too much?

One of the company’s founders has just been moved onto your team. She’s been here forever and seems to have special access to the CEO. Is this a problem or an opportunity?

Your new boss has a habit of directing your staff members without talking to you first. Its sending a confusing message and marginalizing your position. How do you get this to stop?

The landscape of insubordination is complex to say the least. Not all of the situations I’ve listed can be managed the same way. I’m not even sure they’re all necessarily negative. In some of these cases there may even be opportunities hiding under the surface if you play it correctly. What I do know is that in all cases where insubordination is present or probable, there are three things I try to do to give myself the best chance of coming out on top. These tactics are by no means guarantees – insubordination is a messy business – but they will improve your odds.

One of the things you’ll immediately notice about my favorite tactics is that they’re not defensive. They’re not predictable either. My observation of most managers is that they almost universally respond to the slightest hint of insubordination with a full frontal assault. They get pissed. They get defensive. They get paranoid. And they almost always make things worse. The sad reality is in many cases of insubordination, especially those where a team member has a special relationship with your boss or a superior, you don’t have as much actual leverage as you think you do (or should). That’s why so many of us end up even more frustrated when we get nowhere after complaining to the boss about their old college buddy circumventing the chain of command. Sure there are some cases where you can snuff out insubordination using your legitimate authority. If you’ve got an ambitious team member who likes to skip you and jump straight to your boss, you can deal with it head on and your boss will support you. But when that ambitious team member is also your boss’s nephew, you need to get more creative.

Here are my three best tactics for handling an insubordinate employee when a conventional strategy won’t work:

Threesome? Our natural reaction to insubordination is to fight back. We try to restrict their access to the boss. We try to stop the bad behavior by playing defense. Unfortunately, this approach rarely works and it can make you look petty and paranoid if you’re not careful. In my experience, it can be much more effective to take the complete opposite approach. Rather than trying to stop the employee from having secret meetings and private powwows with your boss, why not join them? Why not create more opportunities for the three of you to meet? Why not take the secret dialogue between the two of them and turn it into a three way? There are a lot of positives that can come from this counter intuitive approach:

By building more three-way discussion you curb the secret dialogue and get to participate.

Instead of seeming paranoid and defensive you seem confident and supportive.

With a stronger three-way bond your boss will be less likely to want to engage without you.

My advice to managers when dealing with insubordination is to consider leaning in instead of being defensive. Find ways to actively encourage more three-way dialogue to make a private 1 on 1 relationship seem unnecessary.

Shine a light. Another tendency for managers when struggling with insubordinate behavior is to deal with it too quietly. We talk about it in whispers and complain about it to our spouses and colleagues instead of casting a light on it. The problem is, when you fight against surreptitious behavior with your own surreptitious behavior, the result is, more often than not, pestilential paranoia and a complete lack of trust. Why not take the opposite approach? Why not bring everything out into the open? Why not sit down with the insubordinate employee and have a positive conversation about the situation? I’m not talking about telling her all the reasons you’re pissed either. I’m suggesting you sit down with her and have a conversation about how her special relationship with your boss must be challenging for everyone … including her. I’m suggesting you dial down the paranoia and ratchet up the empathy. Several good things can come of this:

By putting everything out on the table you’re delivering a message without having to fight.

By having a positive conversation vs attacking or accusing, you will be seen as a leader.

By recognizing the challenging situation she’s in, you demonstrate empathy and build trust.

My advice to managers is to combat covert insubordination by bringing everything into the open in a positive way. Start talking about the situation without attacking it. In my experience you’ll find this approach goes a long way to containing negative insubordinate behavior.

Silver Linings Playbook. As managers, we tend to fixate on the negative aspects of insubordination and completely ignore the potential positives. Obviously many, if not most cases of insubordination don’t bring opportunities - but some do. Especially cases where your insubordinate employee is a relative or close friend with your boss or superior. In these cases, you can actually make the insubordinate relationship work in your favor. Why not use this special access to further your own relationship with your superior? Why not draft off any favoritism to help get your team’s projects sponsored and implemented? Why not team up with your special team member instead of going to war? In my experience we’re too quick to go nuclear when insubordination is afoot. It can sometimes pay off to take a quick step back and investigate the opportunities of going positive before we go negative. Some benefits of drafting off an employee’s special relationship include:

Get yourself more access to superiors and more face time with your boss.

Get more support for your projects, and more access to budget.

Deal with less criticism for your team’s work and get faster and easier alignment.

My advice to managers is to look at every situation objectively. Don’t get caught up in the emotion of it all. Almost every career situation you face presents an opportunity, this one is no different.

Dealing with insubordination can be really frustrating and its often difficult to know how to handle the situation. I hope these tips were helpful and serve you well when you’re faced with this challenge.